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The crystal structure of 2,4,6-tri­chloro­iodo­benzene, C6H2Cl3I, a precursor of polychlorinated bi­phenyls (PCBs), is described.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803022530/om6179sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803022530/om6179Isup2.hkl
Contains datablock I

CCDC reference: 227002

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.021
  • wR factor = 0.052
  • Data-to-parameter ratio = 20.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C6 H2 Cl3 I
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1994); software used to prepare material for publication: SHELX97-2 (Sheldrick, 1997) and local programs.

2,4,6-Trichloro-1-iodobenzene top
Crystal data top
C6H2Cl3IF(000) = 568
Mr = 307.33Dx = 2.472 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 3.9970 (1) ÅCell parameters from 1946 reflections
b = 21.5840 (4) Åθ = 1.0–27.5°
c = 9.7510 (2) ŵ = 4.76 mm1
β = 100.994 (1)°T = 90 K
V = 825.79 (3) Å3Block, colourless
Z = 40.15 × 0.10 × 0.10 mm
Data collection top
Nonius KappaCCD
diffractometer
1891 independent reflections
Radiation source: fine-focus sealed tube1689 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 18 pixels mm-1θmax = 27.5°, θmin = 1.9°
ω scans at fixed χ = 55°h = 55
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
k = 2727
Tmin = 0.514, Tmax = 0.621l = 1212
3722 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.021Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.052H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0246P)2 + 0.3565P]
where P = (Fo2 + 2Fc2)/3
1891 reflections(Δ/σ)max = 0.001
91 parametersΔρmax = 0.88 e Å3
0 restraintsΔρmin = 0.84 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.86618 (4)0.144598 (8)0.012742 (16)0.01723 (8)
Cl10.70450 (17)0.00855 (3)0.15938 (7)0.02172 (15)
Cl20.08073 (17)0.10503 (3)0.61485 (6)0.02019 (15)
Cl30.46807 (17)0.25731 (3)0.19849 (6)0.02093 (15)
C10.5709 (6)0.13230 (12)0.1860 (3)0.0146 (5)
C20.5200 (6)0.07368 (12)0.2463 (3)0.0152 (5)
C30.3201 (6)0.06479 (12)0.3776 (3)0.0167 (5)
H30.28820.02450.41710.020*
C40.1679 (6)0.11593 (12)0.4500 (3)0.0153 (5)
C50.2122 (6)0.17501 (12)0.3950 (3)0.0152 (5)
H50.10700.20960.44600.018*
C60.4145 (6)0.18255 (12)0.2634 (3)0.0147 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.01488 (11)0.02496 (12)0.01033 (11)0.00102 (6)0.00139 (7)0.00023 (6)
Cl10.0267 (4)0.0185 (3)0.0174 (3)0.0049 (3)0.0022 (3)0.0043 (2)
Cl20.0266 (4)0.0204 (3)0.0107 (3)0.0007 (3)0.0035 (2)0.0005 (2)
Cl30.0293 (4)0.0157 (3)0.0158 (3)0.0012 (3)0.0005 (3)0.0029 (2)
C10.0126 (12)0.0224 (13)0.0084 (12)0.0012 (10)0.0013 (9)0.0007 (10)
C20.0146 (12)0.0173 (13)0.0138 (12)0.0021 (10)0.0032 (9)0.0049 (10)
C30.0211 (13)0.0146 (12)0.0148 (12)0.0014 (10)0.0043 (10)0.0005 (10)
C40.0164 (13)0.0204 (13)0.0082 (12)0.0029 (10)0.0002 (9)0.0013 (10)
C50.0169 (13)0.0172 (13)0.0113 (12)0.0012 (10)0.0020 (10)0.0031 (10)
C60.0164 (13)0.0159 (13)0.0124 (12)0.0026 (10)0.0039 (10)0.0025 (10)
Geometric parameters (Å, º) top
I1—C12.085 (3)C2—C31.387 (4)
Cl1—C21.732 (3)C3—C41.387 (4)
Cl2—C41.737 (2)C3—H30.9500
Cl3—C61.732 (3)C4—C51.381 (4)
C1—C21.394 (4)C5—C61.390 (3)
C1—C61.399 (4)C5—H50.9500
C2—C1—C6117.5 (2)C5—C4—C3121.7 (2)
C2—C1—I1121.27 (18)C5—C4—Cl2119.5 (2)
C6—C1—I1121.22 (18)C3—C4—Cl2118.8 (2)
C3—C2—C1121.8 (2)C4—C5—C6118.4 (2)
C3—C2—Cl1117.1 (2)C4—C5—H5120.8
C1—C2—Cl1121.06 (19)C6—C5—H5120.8
C2—C3—C4118.6 (2)C5—C6—C1121.9 (2)
C2—C3—H3120.7C5—C6—Cl3117.1 (2)
C4—C3—H3120.7C1—C6—Cl3120.92 (19)
C6—C1—C2—C30.5 (4)C3—C4—C5—C60.2 (4)
I1—C1—C2—C3179.05 (19)Cl2—C4—C5—C6179.49 (19)
C6—C1—C2—Cl1179.65 (18)C4—C5—C6—C10.3 (4)
I1—C1—C2—Cl10.8 (3)C4—C5—C6—Cl3179.36 (18)
C1—C2—C3—C40.0 (4)C2—C1—C6—C50.7 (4)
Cl1—C2—C3—C4179.85 (19)I1—C1—C6—C5178.90 (19)
C2—C3—C4—C50.4 (4)C2—C1—C6—Cl3178.98 (19)
C2—C3—C4—Cl2179.64 (19)I1—C1—C6—Cl31.4 (3)
 

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